Rook’s Guide to Break Into Tech Sales #2: Anthropic

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This is my ongoing series where I identify, highlight, and provide a guide on how I’d break into different tech sales organizations.

This will range from pre-seed startups to some of the hottest & biggest companies on the market. It’s a guide that I wish I had when I was figuring out how to break into tech sales.

If you missed the first edition check it out here:
Rook’s Guide to Break Into Tech Sales #1: Vercel

As you are probably well aware, Anthropic is one of the hottest companies in the world right now. I wanted to pick a top-tier company for this one edition.

For complete transparency, Anthropic is probably the hardest company that will ever be chosen in this series to break into. But, nonetheless, if I wanted to switch companies & break into Anthropic this is how I would do it.

With AI booming & almost all modern companies attempting to implement (& even build their own products) AI into their workflows, the talent attraction & density at Anthropic is going to be massive.

This will take a very calculated & proactive person to break in.

However, that is tech sales. Land at the right spot & your life can change forever.

Now that we’ve identified a promising org, it is time for step 2.

Is the org even actively hiring?

I took a quick look at Anthropic’s career page & found something super interesting.

This is why I’m so bullish on sales… because they have more open sales positions than any other job type currently.

I dug a little deeper and we are in business. Plenty of open AE roles for those looking to change companies, but this is mainly for my folks looking to break into tech sales.

There are open BDR roles. Hybrid in San Francisco or New York City. OTE $116-131k

As you know, it is now time to apply. Always apply to jobs directly through the companies job posting.

I wrote about some application & resume tips a few weeks ago here:
Why You’re Not Getting SDR Interviews

This dives into greater detail when it comes to applying, how to setup your resume, passing the AI resume filter test, etc.

Now that we have applied & submitted our application for the BDR role, it is time to get our foot in the door. This is a must. Any job at Anthropic is going to be flooded with job thousands of applicants.

Typically like all outreach - it starts with searching on LinkedIn. It’s now time to ‘do the job to get the job.’

My first search / filter recommendation always is to try & find people that went to the same university as you. Unless you went to college to do something in medicine, law, or science - then the main benefit of college is just the network that it provides you.

For example, say you went to Penn State - I’d be reaching out to all 19 of these folks that went to Penn State & currently work at Anthropic.

I understand that they likely aren’t in the role you want… however it is called multi-threading.

Find any way in you can at the company & maybe your new PSU friend can introduce you to someone on the sales team. Make sense?

The next few searches I’d be making are:
GTM Recruiter
BDR Manager / Director
BDR
AE, etc.

Plenty of good resources here:

Anthropic has around ~5,000 employees. If you still can’t find people that would make sense to reach out to then hit me up. I can help.

Keep the messaging simple, but super relevant. Tie it back to why Anthropic specifically.
Let them know you’ve applied. And a few brief reasons on why you’d make a great fit.

This is where it will be super important to say that you’ve spoken to other folks at Anthropic too.

This will need to be done over LinkedIn, email, and cold calling. Yes, you are going to need to cold call for a company like Anthropic. That is what will separate you from 97% of applicants.

In a few weeks - I’ll send out an email / article on the type of messaging you should be sending to current BDRs / AEs / Managers / Recruiters to get conversations / referrals.

I always suggest a 15 minute phone call. It is a much lighter ask for people out of their busy days. It goes quick - so you need take advantage of it.

Typically, I like to make some small talk to begin. Could be about anything, but build some rapport.

Then right after that dive in. Ask smart questions: product direction, company goals, growth, state of the sales org, etc.

Some example questions I’d ask:
-”Where are you seeing the most traction right now - startups building on top of Claude, or larger enterprises integrating it into workflows?”
-“How has the GTM motion evolved over the past 6–12 months as the AI market has matured?”
-”From our conversation, I’m even more interested - would you recommend I speak with anyone else on the team or would you be open to referring me to the role?”

These aren’t basic questions - and show that you are prepared & care.

Plus, if you can get someone to refer you internally that is how you will get an interview.

Don’t be shy to ask - companies give referrals bonuses & that is how you will actually break in.

This is the framework you need to adopt to land interviews at tech companies.

Identify company → research → apply → outreach → referral → interview

The market is tough. There are thousands of applicants to every open role. You need to stand out & have someone refer you internally. Do what others won’t.

Until next week.

– Rook ♜

ps… are you looking to break into tech sales & need help? I offer help here